Cat in the Cradle (Or in Felicity's Apartment)
by thatmasquedgirl
Summary: AU: Pineapple Investigations, #1. *It's not easy being Oliver's best friend. Especially when he gets one of his ideas.* Another way Oliver and Felicity could have found found each other, this time featuring hare-brained schemes, 57 jobs, and a cat named Mrs. Pickles. No island, no vigilantes. Just a Psych AU. (Yes, you read that right.) Prompt fic. Complete.


**Title: Cat in the Cradle (Or in Felicity's Apartment)  
Word Count: 1817**

 **Prompt: I asked, " _I'm feeling write-y this evening, but with no direction. Anyone have a short subject prompt for me?_ " Bushlaboo replied: " _I usually answer pineapple to these things, even though I don't like the fruit._ "**

 **Notes:** If your first question is "WTF, Masque?" my answer is, "I honestly have no idea."

Sadly, there are no pineapples in this fic, but after seeing that single word, I immediately thought of Psych. I never discovered how much of a problem I had until this prompt happened. My family is _obsessed_. (Like, every time there is a pineapple, someone is obligated to yell, "I FOUND THE PINEAPPLE!" which leads to a lot of weird looks at the grocery store.) So I guess I was exhausted/punchy enough today to give this a go.

(For those of you wondering, there was a long-running pineapple gag on Psych, where the actors worked to put a pineapple in every episode. There was even a sweepstakes you could enter by finding the hidden pineapple in every episode.)

To be honest, Oliver is crazily out of character for canon!Oliver. But since I'm eliminating the island, I prefer to think of it as an alternate version of pre-island!Oliver who grew up in his relatively normal household.

If God is with me, I will never descend into this kind of madness again.

Thank you for reading. I'm dying to hear your thoughts on this utter insanity, should you have the time. Thanks for being awesome! :)

* * *

"Hey, Smoak, I've got a proposition for you."

She jumps at the sudden sound of Oliver's voice at the door of her office, and her mouth immediately turns to a frown. God, how many bad decisions have started with those words? Too many to count. And now he's in her office in the IT department of Queen Consolidated _yet again_ , with that cocksure grin that's spelled out doom so many times before. As always, he comes back because when has she ever been able to deny him anything?

Utterly and totally oblivious to the things that matter, Oliver drops into a seat across from her desk, slouching as though he's preparing to put his feet on the desk. Again. He's all boyish charm, as always, wearing that same leather jacket and the boots she knows only go with his too-expensive motorcycle. If trouble had a name, it would be Oliver Queen in every way, right down to that roguish grin.

"Must be a slow day," he observes, nodding toward her, "if you're playing _World of Warcraft_."

Really, she shouldn't be amazed anymore. He's been this sharp ever since they were kids—since she was the awkward scholarship student who skipped four grades and he was the prep school's resident troublemaker. They shouldn't have clicked, but they did—probably because underneath that flighty, fun-loving exterior was the same guy who helped her study for calculus exams at MIT.

When she gapes at him and the screen he can't see, he only shrugs and rolls his eyes. "Please, Smoak." He nods toward her hands on the keyboard. "Left hand arrow keys, right hand mouse?" He drapes an arm over the back of the chair. "You should at least _try_ to make it a challenge for me."

She huffs a long-suffering sigh that both of them know she doesn't mean. "While I appreciate you have nothing to do with your idle rich ass," she answers with a lopsided smile, "I actually have a job to do. One that I _earned_ , despite the fact your name is on the building. You can't just waltz in here and take over my office."

He only leans forward over the desk. "I had a weird day today," he proclaims, getting straight to the point. His head tilts to the side. "Remember when I called you last night? I hooked up with that girl from the bar and—"

Yeah, no. She is _not_ doing this. There are only a few things that Felicity and Oliver don't talk about, but this is one of them. "Shouldn't you be having this conversation with Tommy?" Rounding out their small group of misfits in high school was Tommy Merlyn, Oliver's favorite wingman.

Waving her off with a hand, he levels a look. "Since when do you have trust issues?" He points to himself. "Do you not remember who helped you move across country to MIT when your mom threw a fit?"

Felicity offers no mercy. "I also seem to remember you ditching me in Boston to get laid."

"That…" he starts, indignant. She only quirks an eyebrow in reply, daring him to deny it. "That is _such_ an inconvenient thing for you to remember right now," Oliver finally sputters. He waves a hand. "But what I was _going_ to say is that after I got back to my apartment, things started to progress, and…" He makes a face. "She hit the remote, and the news came on, so I called in a quick tip on those stereo robberies all over the news." Felicity snorts; _there's_ her Oliver, the one who would turn down his kryptonite—a woman—just for a chance to show off.

"But Lance pulls me down to the police station," he continues. Felicity groans, thinking that the least he could do is stay away from his ex-girlfriend's dad. Or maybe _ex-girlfriends'_ dad. One thing has never changed: it's always an exercise in semantics with Oliver. "Stereo robber had an accomplice, so of course Lance thinks it's me." He lifts a shoulder. "So I just pretended to be a psychic."

The pause that follows brings new meaning to the phrase _silent as the grave_ while Felicity waits for the punch line. Instead, he leans forward with that heart-stopping grin and drums across the top of her desk. "We're going to open a private detective agency!"

Though his smile is so beautiful, it's Felicity's job as the realist in this friendship to point out the horrible flaws. Pushing away from her computer, she rounds her desk to lean against it, staring down at him. "Oliver," she starts slowly, "you know I love you—"

"You say that," he teases, pointing a finger at her, "but you don't mean it."

Felicity ignores him. "—but this may be the worst idea you've ever had. And that is saying something." She pokes him in the chest. "Also, I am never, _ever_ taking a job with you again. I learned that at the Mexican border. _Twice_."

He rolls his eyes during an exaggerated sigh, as if _she's_ the difficult one. God forbid she has a stable job and a college degree and a normal life. "Name one bad job I've worked," he challenges. Felicity only arches an eyebrow, and motions her on. "Come on. Name one."

"Haunted house," she answers without missing a beat.

He touches his nose. "In my defense, I didn't know you were easily scared and have a mean right hook."

"Planetarium," Felicity tries again.

Defensively, he replies, "It wasn't spinning _that_ fast. I can't help it if a few people got motion sickness."

"The acupuncture clinic."

"I didn't realize experience was necessary, Smoak."

"What about the summer you spent driving the Oscar-Meyer wiener mobile?"

Judging by the look on his face, he would have been less affronted if she'd insulted his mother. "I did that for the free hot dogs," he answers, as though it's a perfectly rational explanation.

"I can't do this with you right now," Felicity declares, shaking her head. "Oliver, you've had fifty-seven jobs since we left high school. You never date the same woman for more than two weeks. Your life is _wildly_ unstable." He only blinks at her. "I know you see that as a good thing—and God knows I would _never_ try to change you. But I _need_ this job. I need to have a nine-to-five job with health coverage, retirement plans, and stock options. I need that just as much as I need a best friend who can't sit still." They share a smile. "I'm sorry, Oliver, but I can't go play psychic detective with you."

He only sighs, deflating, and she feels as though she kicked a puppy. Things were so much easier in high school, when adventure was an exciting prospect and getting out of Starling City was her only desire. Every year separates the two of them a little bit more, with this chasm of differences in the ways they live their lives. Felicity grew up; Oliver didn't.

Somehow she ended up being best friends with Peter Pan.

That didn't work out too well for Wendy.

She sighs, too, a bone-deep exhaustion settling over her. She always knew it would end up like this, but damn it, she let herself do it anyway. Another way high school was easier? Having a crush on her best friend wasn't so complicated. Now she knows it isn't just a crush, but she's always going to be that nerdy blonde girl with the sharp tongue to him. Some days, it's okay. Other days, it feels like she's trying to push a boulder uphill.

"Smoak…" he starts, in that tone.

"No," she snaps immediately. His expression never wavers. " _No_ , Oliver. I mean it. Don't."

In that far too vulnerable voice, he says, "Felicity, I need you. Please."

She knows she's done for. Five little words and she's gone. That's the crux of the problem, isn't it? Whether he recognizes it or not, Oliver _does_ need her. After growing up with all the best nannies and the best parenting substitutes money could buy, Oliver Queen needs this recklessness—just as much as he needs her to pull him back from the edge when he gets too close.

After a decade of being in love with him, Felicity can deny him nothing. She relents with a long breath and a shake of her head. "Fine," she agrees tiredly. "Just today, though, Oliver." He lights up like a kid in a candy store—something she knows from experience, since he's done that job before, too. "And only because I've finished up everything I need to do today."

When Oliver leaps from the chair, it brings them way too close for a few heartbeats. Oliver breaks the spell by taking her coat from the rack, holding it out for her. She slides into it, trying not to relish the way his hands feel on her shoulders.

"I promise you won't regret this," he says, and somehow she already does. He tucks her arm around his, and Felicity tries not to focus on the sensation. That willpower lasts all of two seconds before he kisses her temple, and then she's putty in his hands. Once again, he's played her like a fiddle at an Ozark hoedown. She might actually be angry if she thought he was doing it on purpose, but Oliver is both the most observant and obtuse person she's ever met.

He pats her hand. "By the way, I told Walter you needed off because Mrs. Pickles is sick."

He drags her along for a fraction of a second when she stops short. "Who the hell is Mrs. Pickles?"

Oliver shrugs. "Your cat." His head tilts thoughtfully. "Though I'm not sure cats are allowed to marry in Starling City."

It would be an excellent excuse, if she wasn't allergic to cats. "So now I have a cat?" Felicity demands.

He doesn't even skip a beat before answering, "A gray tabby. Last Hanukkah, you made her a sweater with little dreidels all over it."

She rolls her eyes. "Oliver, you are _not_ turning me into a crazy cat lady. Especially not when I'll have to look your stepfather in the eye and lie to him about this. I _do not want_ a female cat named Mrs. Pickles." Her brow furrows. "How did you even come up with that?"

"A male cat wouldn't serve my purposes so well," is his reply. He grins so smugly that Felicity has to fight the urge to slap him. "Did you know that cats go into heat as often as every two weeks and are only pregnant for two months?" His eyes light up with a silent laugh, and she melts. "The next time I need you, Smoak? Pickles is having kittens."

"I hate you," becomes her reply after a moment of stuttering.

He just winks. "Love you, too, Smoak."

* * *

 **Notes:** If you're here, it's because you survived. You are a good, pure soul, and I thank you.


End file.
